Preparation of glycidyl polyarylethers

Abstract

Glycidyl polyarylethers are prepared by reacting at least one alkali metal salt of a polyhydric phenol with at least one 1-halo-2,3-epoxyalkane, in an anhydrous and aprotic heterogeneous reaction medium which includes acetonitrile, propionitrile, benzonitrile and/or ethylene sulfide.

What is claimed is: 
     
       1. In a process for the preparation of a glycidyl polyarylether comprising reacting at least one alkali metal salt of a polyhydric phenol with at least one 1-halo-2,3-epoxyalkane, in an anhydrous and aprotic reaction medium, the improvement which comprises said reaction medium being heterogeneous and including an organic compound selected from the group comprising acetonitrile, propionitrile, benzonitrile and ethylene sulfide. 
     
     
       2. The process as defined in claim 1, wherein the alkali metal cation is selected from the group consisting of sodium, potassium, lithium, cesium, and mixtures thereof. 
     
     
       3. The process as defined by claim 2, wherein said cation is sodium or potassium. 
     
     
       4. The process as defined by claim 3, wherein said cation is sodium. 
     
     
       5. The process as defined by claim 1, wherein said polyhydric phenol is a diphenol. 
     
     
       6. The process as defined by claim 1, wherein said polyhydric phenol is selected from the group consisting of 1,2-dihydroxybenzene, 1,3-dihydroxybenzene, 1,4-dihydroxybenzene, 1-2-dihydroxy-4-chlorobenzene, 1,2-dihydroxy-4-bromobenzene, 1,2-dihydroxy-3-methylbenzene, 1,3-dihydroxy-5-chlorobenzene, 1,3-dihydroxy-5-bromobenzene, 1,3-dihydroxy-2-methylbenzene, 1,4-dihydroxy-2-chlorobenzene, 1,2,3-trihydroxybenzene, 1,2,4-trihydroxybenzene, 1,2,5-trihydroxybenzene, 1,3,5-trihydroxybenzene, 1,2-dihydroxynaphthalene, 1,4-dihydroxynaphthalene, 1,5-dihydroxynaphthalene, 2,3-dihydroxynaphthalene, 1,2-dihydroxyanthracene, 1,2,9-trihydroxyanthracene, 1,4,9-trihydroxyanthracene, 1,2,10-trihydroxyanthracene, 4,4'-dihydroxydiphenyl, 4,4'-dihydroxydiphenylsulfone, 2,3-dihydroxydiphenylsulfone, 2,4,2',4'-tetrahydroxydiphenyl, 2,4,2',5'-tetrahydroxydiphenyl, 2,5-dihydroxydiphenylmethane, 4,4'-dihydroxydiphenylmethane, 1,1-bis(4-hydroxyphenyl)ethane, 1,1-bis(4-hydroxyphenyl)isobutane, 2,2-bis(4-hydroxyphenyl)propane, 2,2-bis)4-hydroxyphenyl)butane, 2,2-bis(4-hydroxy-2-methylphenyl)propane, 2,2-bis(2-hydroxy-4-tertbutylphenyl)propane, 2,2-bis(2-hydroxyphenyl)propane, 2,4'-dihydroxydiphenyldimethylmethane, 2,2-bis(2-chloro-4-hydroxyphenyl)propane, 2,2-bis(4-hydroxyphenyl)-1,1,1-trichloroethane, 2,2-bis(4-hydroxyphenyl)-1,1-dichloroethylene, tris(4-hydroxyphenyl)methane, 2,2,3,3-tetrakis(4'-hydroxyphenyl)butane, 2,2,4,4-tetrakis(4'-hydroxyphenyl)pentane, 2,2,5,5-tetrakis(4'-hydroxyphenyl)hexane, 1,1,2,2-tetrakis(p-hydroxyphenyl)ethane, and 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane. 
     
     
       7. The process as defined by claim 1, wherein said polyhydric phenol is a novolak resin. 
     
     
       8. The process as defined by claim 1, wherein said polyhydric phenol is selected from the group consisting of 1,2-dihydroxybenzene, 1,4-dihydroxybenzene, bisphenol A, bisphenol F, 2,2-bis(4-hydroxyphenyl)-1,1-dichloroethylene, and 2,2-bis(3,5-dibromo-4-hydroxyphenyl)propane. 
     
     
       9. The process as defined by claim 8, wherein said polyhydric phenol is bisphenol A, bisphenol F, or mixtures thereof. 
     
     
       10. The process as defined by claim 9, wherein said polyhydric phenol is bisphenol A. 
     
     
       11. The process as defined by any of claims 1, 6 or 8, wherein said 1-halo-2,3-epoxyalkane is selected from the group consisting of 1-chloro-2,3-epoxypropane, 1-bromo-2,3-epoxypropane, 1-chloro-2,3-epoxybutane, 1-chloro-2-methyl-2,3-epoxypropane, and mixtures thereof. 
     
     
       12. The process as defined by claim 11, wherein said 1-halo-2,3-epoxyalkane is epichlorohydrin. 
     
     
       13. The process as defined by claim 1, wherein the reaction is conducted in the presence of 1 to 13 moles of 1-halo-2,3-epoxyalkane per gram equivalent of --OM groups comprising the polyhydric phenol, with M being the alkali metal cation. 
     
     
       14. The process as defined by claim 13, there being present 1 to 5 moles of the 1-halo-2,3-epoxyalkane. 
     
     
       15. The process as defined by claim 1, the organic compound being anhydrous acetonitrile. 
     
     
       16. The process as defined by claim 1, the organic compound being anhydrous propionitrile. 
     
     
       17. The process as defined by claim 1, the organic compound being anhydrous benzonitrile. 
     
     
       18. The process as defined by claim 1, the organic compound being anhydrous ethylene sulfide. 
     
     
       19. The process as defined by claim 1, the organic compound comprising from 10 to 80% by weight of the reaction medium. 
     
     
       20. The process as defined by claim 1, the organic compound comprising at least 30% by weight of the reaction medium. 
     
     
       21. The process as defined by claim 1, the reaction being conducted at a temperature of from 50° to 150° C. 
     
     
       22. The process as defined by claim 1, comprising reacting the disodium salt of bisphenol A with epichlorohydrin, at the rate of 2 to 10 moles of epichlorohydrin per mole of the bisphenol A salt, in a reaction medium including 30 to 80% by weight acetonitrile, and at a temperature of from 80° to 120° C. 
     
     
       23. The process as defined by claim 1, further comprising filtering the mixture of reaction to remove the alkali metal halide formed during the course of the reaction, distilling the filtrate to remove unreacted 1-halo-2,3-epoxyalkane and the organic compound comprising the reaction mixture, and recovering the product glycidyl polyarylether.